Reissert compound chemistry. Part 5. Formation of pyrrolo[1,2-a]-quinolines and pyrrolo[2,1-a]isoquinolines

Abstract

Treatment of a quinoline Reissert compound carrying a blocking group at the 4-position with base in the presence of acrylonitrile can lead in modest yield to the pyrrolo[1,2-a]quinoline system (8) and to an open chain ketone (11) derived via an intermediate tetrahydropyrrolo[1,2-a]quinoline. This behaviour contrasts with the more ready formation of the pyrrolo[2,1-a]isoquinoline system (3) by a similar process.